Porous diacetylene particles, synthesis method thereof

ABSTRACT

Provided are a radial porous diacetylene particle, which is synthesized by ion-bonding a diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 above with a diamine or dicarboxylic acid monomer represented by Formula 2 above, and a method of manufacturing the same.

CROSS REFERENCE TO RELATED APPLICATION

This application claims the benefit of Korean Patent Application No. KR10-2011-0054777, filed Jun. 7, 2011, which is hereby incorporated byreference in its entirety into this application.

BACKGROUND OF THE INVENTION

1. Technical Field

The present invention relates to a porous diacetylene particle, and,more particularly, to a method of synthesizing a novel porousdiacetylene particle having optical characteristics using adiacetylene-containing dicarboxylic acid or diamine monomer and adiamine or dicarboxylic acid monomer.

2. Description of the Related Art

Generally, a sensor material used in a biosensor requires highselectivity and sensitivity to a target material to be detected. Forthis reason, an enzyme and an antibody have been generally used as amatrix of a biosensor, but they are disadvantageous in that stabilitybecomes poor when they are fixed in the biosensor, and in that they areexpensive. Therefore, research into synthetic biosensors imitating thefunction of a biomaterial such as an enzyme or an antibody has beenactively conducted. Polydiacetylene (PDA), which is an organic materialused in such a biosensor, is generally used to detect chemical andbiological materials because it has specific color characteristics.

Polydiacetylene (PDA) is a conjugate polymer, and is receivingconsiderable attention in several viewpoints. First, polydiacetylene(PDA) is generally prepared by irradiating self-assembled diacetylenesupermolecules with UV. Second, when PDA is prepared under an optimumcondition, it has a dark blue color having a maximum absorptionwavelength of 640 nm Third, blue PDA is changed into red PDA (maximumabsorption wavelength of 550 nm) depending on environmental stimuli.Owing to the change of blue PDA into red PDA, various chemical sensorsbased on PDA have been developed. Therefore, it was reported that, sincepolydiacetylene (PDA) is optically characterized in that its color ischanged depending on heat, Ph, physical or chemical stimuli or molecularrecognition, it is used to detect the colors of biologically, chemicallyand environmentally important target materials such as DNA, viruses,proteins, metal ions, organic solvents, etc.

As a conventional polydiacetylene sensor, a sensor having a vesiclestructure in which a film and a vesicle solution are fixed on asubstrate has been used This vesicle-type sensor is problematic in thatthe time required to detect a target material is not short and theaccuracy required to detect the target material is not high because itsfluorescent intensity is not high and the target material is not easilydiffused. Further, the vesicle-type sensor is problematic in thatsamples must be treated cautiously because it is sensitive to thermalstimuli.

In the present invention, porous particles having a large surface areawere prepared such that the diffusion efficiency of a target material tobe detected is increased and the time required to detect the targetmaterial is decreased, and new monomers were introduced such that thefluorescent intensity of a sensor is improved and the sensor is notsensitive to thermal stimuli.

SUMMARY OF THE INVENTION

Accordingly, the present invention has been devised to solve theabove-mentioned problems, and an object of the present invention is toprovide a radial porous diacetylene particle and a method ofsynthesizing a radial porous diacetylene particle having opticalcharacteristics using a diacetylene-containing dicarboxylic acid ordiamine monomer and a diamine or dicarboxylic acid monomer.

In order to accomplish the above object, the present invention providesa radial porous diacetylene particle, which is synthesized byion-bonding a diacetylene-containing dicarboxylic acid or diaminemonomer with a diamine or dicarboxylic acid monomer.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other objects, features and advantages of the presentinvention will be more clearly understood from the following detaileddescription taken in conjunction with the accompanying drawings, inwhich:

FIG. 1 is a schematic view showing the formation of radial porousdiacetylene particles according to the present invention;

FIG. 2 is a graph showing the results of analyzing the formationmechanism of the radial porous diacetylene particles using FTIR;

FIG. 3 is photographs showing the surface and inner structure of theradial porous diacetylene particles;

FIG. 4 is photographs showing the change of optical characteristics ofthe radial porous diacetylene particles depending on the polymerizationthereof and the thermal stimuli thereto;

FIG. 5 is a graph showing the fluorescent intensity of the radial porousdiacetylene particles relative to the concentration of liquidformaldehyde;

FIG. 6 is a graph showing the results of analyzing the thermal stabilityof the radial porous diacetylene particles using a differential scanningcalorimeter (DSC);

FIG. 7 is photographs showing the results of analyzing the surfacestructure of the radial porous diacetylene particles according to theconcentration of a dicarboxylic acid monomer solution and theconcentration of a diamine monomer solution;

FIG. 8 is photographs showing the results of analyzing the surfacestructure of the radial porous diacetylene particles according to themixing ratio of a dicarboxylic acid monomer solution and a diaminemonomer solution;

FIG. 9 is photographs showing the results of analyzing the surfacestructure of the radial porous diacetylene particles according to thetemperature when mixing a dicarboxylic acid monomer solution and adiamine monomer solution; and

FIG. 10 is photographs showing the results of analyzing the surfacestructure of the radial porous diacetylene particles according to theexistence and nonexistence of a carboxylic acid group, an amine group, adiacetylene group or a benzene group.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, preferred embodiments of the present invention will bedescribed in detail with reference to the attached drawings.

The present invention provides a radial porous diacetylene particle,which is synthesized by ion-bonding a diacetylene-containingdicarboxylic acid or diamine monomer represented by Formula 1 below witha diamine or dicarboxylic acid monomer represented by Formula 2 below:

G-(A)_(x)-C≡C—C≡C—(B)_(y)-G   [Formula 1]

wherein A and B are each independently selected from a substituted orunsubstituted alkyl group of two or more carbon atoms, an ethylene oxidegroup, an amide group and an ester group, G is selected from COOH andNH₂, and x and y are each independently an integer of 1 to 20,

Q-(D)_(m)-Z-(E)_(n)-Q   [Formula 2]

wherein Z is selected from a substituted or unsubstituted alkyl group ofone or more carbon atoms, a benzene group, a cycloalkyl group, apyridine group, a pyrimidine group and a naphthalene group, D and E areeach independently selected from a substituted or unsubstituted alkylgroup of one or more carbon atoms, a benzene group, a cycloalkyl group,a pyridine group, a pyrimidine group and a naphthalene group, D, E and Zare different from each other, Q is selected from COOH and NH₂, m and nare each independently an integer of 0 to 20, and G of Formula 1 aboveis different from Q of Formula 2 above.

The diacetylene-containing dicarboxylic acid or diamine monomers havingboth hydrophilic and hydrophobic property can be formed into varioustypes of Supramolecule (Langmuir-Blodgett film, Langmuir-Schafer film,Lamellar film, vesicle solution, vesicle fixed on substrate, etc.) byself assembly. When the diacetylene-containing dicarboxylic acid ordiamine monomers are spaced apart from each other at regular intervals,they are exposed to UV (254 nm) to be polymerized, have a blue color,and do not reveal a fluorescence. The reason why polydiacetylene has ablue color is because π electrons in the main chain thereof absorb lighthaving a wavelength of 640 nm. When the length of a covalent bond of πelectrons of polydiacetylene is decreased by heat, pH, physical orchemical stimuli or molecular recognition, the color thereof is changedfrom blue to red, thus revealing a self fluorescence. The radial porousdiacetylene particle of the present invention has opticalcharacteristics of color transition and fluorescence-emitting throughthis mechanism

Here, the diamine or dicarboxylic acid monomer represented by Formula 2may include a benzene ring. More preferably, this diamine ordicarboxylic acid monomer may be represented by Formula 3 below:

Q-(H₂C)_(m)-C₆H₄-(CH₂)_(n)-Q   [Formula 3]

-   -   wherein Q is selected from COOH and NH₂, and m and n are each        independently an integer of 1 to 10.

The radial porous diacetylene particle of the present invention issynthesized by ion-bonding the diacetylene-containing dicarboxylic acidor diamine monomer represented by Formula 1 above with the diamine ordicarboxylic acid monomer represented by Formula 2 above to form aradial porous diacetylene particle and then growing the radial porousdiacetylene particle. Concretely, a carboxylic acid group was radiallyion-bonded with an amine group, so that radial porous diacetyleneparticles having specific porosity are formed and grown by interactionssuch as the Van der Waal's force between carbon chains and the π-π bondbetween benzene rings, respectively.

The radial porous diacetylene particle of the present invention ision-bonded and grown to form pores having a large surface area.

The particle size of the radial porous diacetylene particle is 50 nm˜50μm, preferably, 1 μm˜10 μm.

The pore size of the radial porous diacetylene particle is 1 nm˜1 μm,preferably, 2 nm˜100 nm

The present invention provides a method of manufacturing a radial porousdiacetylene particle, comprising the steps of:

(a) respectively dissolving a diacetylene-containing dicarboxylic acidor diamine monomer represented by Formula 1 below and a diamine ordicarboxylic acid monomer represented by Formula 2 below in a solvent toprepare a solution including the diacetylene-containing dicarboxylicacid or diamine monomer and a solution including the diamine ordicarboxylic acid monomer:

G-(A)_(x)-C≡C—C≡C—(B)_(y)-G   [Formula 1]

wherein A and B are each independently selected from a substituted orunsubstituted alkyl group of two or more carbon atoms, an ethylene oxidegroup, an amide group and an ester group, G is selected from COOH andNH₂, and x and y are each independently an integer of 1 to 20,

Q-(D)_(m)-Z-(E)_(n)-Q   [Formula 2]

wherein Z is selected from a substituted or unsubstituted alkyl group ofone or more carbon atoms, a benzene group, a cycloalkyl group, apyridine group, a pyrimidine group and a naphthalene group, D and E areeach independently selected from a substituted or unsubstituted alkylgroup of one or more carbon atoms, a benzene group, a cycloalkyl group,a pyridine group, a pyrimidine group and a naphthalene group, D, E and Zare different from each other, Q is selected from COOH and NH₂, m and nare each independently an integer of 0 to 20, and G of Formula 1 aboveis different from Q of Formula 2 above;

-   -   (b) ultrasonically treating each of the solutions;    -   (c) maintaining each of the ultrasonically-treated solutions at        room temperature; and    -   (d) mixing the solution including the diacetylene-containing        dicarboxylic acid or diamine monomer represented by Formula 1        above with the solution including the diamine or dicarboxylic        acid monomer represented by Formula 2 above to form a radial        porous diacetylene particle and then growing the radial porous        diacetylene particle.

The solvent used may be selected without limitation if it is generallyused in the related field. Preferably, the solvent may be at least oneselected from the group consisting of tetrahydrofuran (THF), chloroform,toluene, ethanol, isopropanol, and n-hexane, and more preferably, thesolvent may be tetrahydrofuran (THF).

The concentration of the solution including the diacetylene-containingdicarboxylic acid or diamine monomer represented by Formula 1 above maybe 10 mM˜50 mM, and the concentration of the solution including thediamine or dicarboxylic acid monomer represented by Formula 2 above maybe 10 mM˜50 mM. More preferably, the concentration of the solutionincluding the diacetylene-containing dicarboxylic acid or diaminemonomer represented by Formula 1 above may be 5 mM˜10 mM, and theconcentration of the solution including the diamine or dicarboxylic acidmonomer represented by Formula 2 above may be 5 mM˜10 mM.

In step (d), when the solution including the diacetylene-containingdicarboxylic acid or diamine monomer represented by Formula 1 above ismixed with the solution including the diamine or dicarboxylic acidmonomer represented by Formula 2 above, it is preferred that theconcentrations of these solutions may be equal to each other, but thepresent invention is not limited thereto.

The ultrasonic treatment may be carried out for 30 minutes by a power of5˜20 W, preferably for 15 minutes by a power of 10˜15 W, and morepreferably for 10 minutes by a power of 10 W.

In step (c), each of the ultrasonically-treated solutions at roomtemperature may be maintained at a room temperature of 5˜30° C. for 10minutes˜1 hour, preferably at a room temperature of 10˜25° C. for 10minutes˜1 hour.

In step (d), the mixing temperature of the solution including thediacetylene-containing dicarboxylic acid or diamine monomer representedby Formula 1 above with the solution including the diamine ordicarboxylic acid monomer represented by Formula 2 above may be 5˜30°C., preferably, 10˜25° C. When the mixing temperature is lower than 5°C., pores are not easily formed, and when the mixing temperature ishigher than 30° C., particles are not easily formed and irregular poresare formed.

It is preferred that the maintaining temperature in step (c) and themixing temperature in step (d) be equal to each other, but the presentinvention is not limited thereto.

In step (d), the solution including the diacetylene-containingdicarboxylic acid or diamine monomer represented by Formula 1 above andthe solution including the diamine or dicarboxylic acid monomerrepresented by Formula 2 above may be mixed in a volume ratio of1:0.2˜5, preferably 1:0.5˜3, and more preferably 1:1.

The method may further include the step of exposing the radial porousdiacetylene particle to UV having a wavelength of 254 nm and applyingthermal stimuli thereto to confirm the specific optical characteristicsof polydiacetylene.

According to the present invention, the size, porosity and opticalcharacteristics of the radial porous diacetylene particle can beadjusted by adjusting the diacetylene-containing dicarboxylic acid ordiamine monomer represented by Formula 1 above and the diamine ordicarboxylic acid monomer represented by Formula 2 above.

The size and porosity of the radial porous diacetylene particle can beadjusted by adjusting the concentration of each of the solutionsincluding the monomers.

The porosity of the radial porous diacetylene particle can be adjustedby adjusting the mixing ratio of the solutions including the monomers.

The size and porosity of the radial porous diacetylene particle can beadjusted by adjusting the mixing temperature of the solutions includingthe monomers.

Further, the radial porous diacetylene particle can be applied to achemical sensor, a DNA sensor, a protein sensor or a cell sensor byintroducing a receptor into the radial porous diacetylene particles andusing optical characteristics.

Hereinafter, the present invention will be described in more detail withreference to the following Examples. These Examples are set forth onlyto illustrate the present invention, and the scope of the presentinvention is not limited thereto.

EXAMPLE 1 Preparation of Monomer Solutions (DCDDA Solution and pXDASolution)

0.03625 g of DCDDA (10,12-Docosadiynedioic acid) and 0.01362 g of pXDA(p-Xylylene diamine) were respectively dissolved in 10 ml of THF(tetrahydrofuran) in a glass bottle to prepare 10 Mm monomer solutions.Subsequently, each of the monomer solutions was ultrasonically treatedfor 10 minutes by a power of 10 W using an ultrasonic generator, and wasthen maintained at 15° C. for 20 minutes.

EXAMPLE 2 Manufacture of Radial Porous Diacetylene Particle

5 ml of the DCDDA solution and 5 ml of the pXDA solution prepared inExample 1 were mixed at a volume ratio of 1:1 at 15° C. by injecting theDCDDA solution into the pXDA solution using a pipette.

In this case, a carboxylic acid group was radially ion-bonded with anamine group, and thus radial porous diacetylene particles havingspecific porosity were formed and grown by interaction between carbonchains and between benzene rings, respectively.

FIG. 1 is a schematic view showing the formation of such radial porousdiacetylene particles, and FIG. 2 is a graph showing the results ofanalyzing the formation mechanism of the radial porous diacetyleneparticles using FTIR.

The formed radial porous diacetylene particle has a particle size of1˜10 μm and a pore size of 2˜500 nm The results thereof are shown inFIG. 3 by scanning electron microscope (SEM) photographs (left of FIG.3) and transmission electron microscope (TEM) photographs (right of FIG.3).

EXAMPLE 3 Analysis of Optical Characteristics of Radial PorousDiacetylene Particle Depending on Thermal Stimuli

When 4 μl of the radial porous diacetylene particle solutionmanufactured in Example 2 was dropped onto a silicon or glass substrateand then dried, any color was not realized and fluorescence was notrevealed. When the radial porous diacetylene particle was exposed to UVof 254 nm at a rate of 1 mW/cm², this radial porous diacetylene particleis polymerized, thus revealing blue color and not revealing redfluorescence.

When the radial porous diacetylene particle was heated at 110° C. for 36hours, it became red, and revealed red fluorescence. The results thereofare shown in FIG. 4.

EXAMPLE 4 Analysis of Fluorescence of Radial Porous Diacetylene ParticleDepending on the Concentration of an Aqueous Formaldehyde Solution

The polymerized radial porous diacetylene particle of Example 2 wasdropped into an aqueous formaldehyde solution to a concentration of 1 Mto 1 μM by 200 μM. Then, a reaction was carried out for 2 minutes, theunreacted solution was removed using nitrogen, and then red fluorescencewas analyzed. As a result, as shown in FIG. 5, it can be ascertainedthat the fluorescent intensity of the radial porous diacetylene particlewas gradually decreased as the concentration of formaldehyde wasdecreased.

EXAMPLE 5 Analysis of Thermal Stability of Radial Porous DiacetyleneParticle

In order to analyze the thermal stability of the radial porousdiacetylene particle manufactured in Example 2, the radial porousdiacetylene particle was observed using a differential scanningcalorimeter (DSC 2010, manufactured by TA Instruments Corp. in U.S.A).The results thereof are shown in FIG. 6. From FIG. 6, it can beascertained that the radial porous diacetylene particle has excellentthermal stability because its melting point is higher than that of eachof the monomers.

EXAMPLE 6 Analysis of the Changes in Characteristics of Radial PorousDiacetylene Particles Depending on the Concentrations of MonomerSolutions

DCDDA (10,12-docosadiynedioic acid) and pXDA (p-xylylene diamine) wererespectively dissolved in THF (tetrahydrofuran) to prepare DCDDAsolutions having concentrations of 5 mM, 10 mM, 20 mM, 30 mM, 40 mM and50 mM and pXDA solutions having concentrations of 5 mM, 10 mM, 20 mM, 30mM, 40 mM and 50 mM. Thereafter, each of the prepared monomer solutionswas ultrasonically treated for 10 minutes by a power of 10 W using anultrasonic generator, and was then maintained at 15° C. for 20 minutes.Subsequently, the DCDDA solution and the pXDA solution having the sameconcentration were mixed at a volume ratio of 1:1 by injecting the DCDDAsolution into the pXDA solution using a micropipette. Thus, carboxylicacid ions of DCDDA were bonded with amine ions of pXDA to form and growradial porous diacetylene particles.

The size and porosity of the radial porous diacetylene particles formeddepending on the concentration of each monomer solution were measuredusing a scanning electron microscope (SEM) and then observed. Theresults thereof are shown in FIG. 7. As shown in FIG. 7, it can beascertained that radial porous diacetylene particles were not easilyformed when the concentration of each monomer solution was less than 5mM, and that radial porous diacetylene particles were formed but theporosity thereof was low when the concentration of each monomer solutionwas more than 20 mM.

EXAMPLE 7 Analysis of the Changes in Characteristics of Radial PorousDiacetylene Particles Depending on the Mixing Ratio of Monomer Solutions

In order to observe the porosity of radial porous diacetylene particlesdepending on the mixing ratio of a DCDDA solution and a pXDA solution,the DCDDA solution and pXDA solutions prepared in Example 1 wererespectively mixed at mixing ratios of 1:3, 1:2, 1:1, 2:1 and 3:1. Inthis case, the DCDDA solution and the pXDA solution were mixed byinjecting the DCDDA solution into the pXDA solution using a micropipetteto form and grow radial porous diacetylene particles.

The radial porous diacetylene particles formed by using different mixingratios of the monomer solutions were measured using a scanning electronmicroscope (SEM) and then observed. The results thereof are shown inFIG. 8. As shown in FIG. 8, it can be ascertained that the pore size ofradial porous diacetylene particles was increased as the ratio of pXDAwas increased at the time of mixing, and that the pore sizes thereofbecame irregular and the pores thereof were not easily formed as theratio of DCDDA was increased.

EXAMPLE 8 Analysis of the Changes in Characteristics of Radial PorousDiacetylene Particles Depending on the Mixing Temperature of MonomerSolutions

0.03625 g of DCDDA (10,12-Docosadiynedioic acid) and 0.01362 g of pXDA(p-Xylylene diamine) were respectively dissolved in 10 ml of THF(tetrahydrofuran) in a glass bottle to prepare 10 Mm monomer solutions.Subsequently, each of the monomer solutions was ultrasonically treatedfor 10 minutes by a power of 10 W using an ultrasonic generator, and wasthen maintained for 20 minutes at 5, 10, 15, 20, 25 and 30° C.,respectively. Subsequently, the DCDDA solution and the pXDA solutionwere mixed at a volume ratio of 1:1 at 5, 10, 15, 20, 25 and 30° C.,respectively. In this case, the DCDDA solution and the pXDA solutionwere mixed by injecting the DCDDA solution into the pXDA solution usinga micropipette to form and grow radial porous diacetylene particles.

The maintenance temperature and mixing temperature were equal to eachother.

The radial porous diacetylene particles formed depending on the mixingtemperature of the monomer solutions were measured using a scanningelectron microscope (SEM) and then observed. The results thereof areshown in FIG. 9. As shown in FIG. 9, it can be ascertained that theradial porous diacetylene particles were not easily formed at 30° C. ormore, that the radial porous diacetylene particles were not easilyformed and the pore sizes thereof became irregular at more than 25° C.,and that the pores thereof were not easily formed at less than 10° C.

EXAMPLE 9 Analysis of the Changes in characteristics of Radial PorousDiacetylene Particles Depending on Whether or not a Cathoxylic acidGroup, an Amine Group, a Diacetylene Group or a Benzene Group was Used

DCDDA (10,12-Docosadiynedioic acid) having two cathoxylic acid groupsand a diacetylene group, TCDA (10,12-Tricosadiynoic acid) having onecarboxylic acid group and a diacetylene group, DCDA (Docosanedioic acid)having two carboxylic acid group, pXDA (p-Xylylene diamine) having twoamine groups and a benzene group, HMDA (Hexamethylenediamine) having twoamine groups, EBA (4-Ethyl-benzylamine) having one amine group and abenzene group and DEB (1,4-Diethyl-benzene) having a benzene group wererespectively dissolved in THF (Tetrahydrofuran) to prepare 10 mM monomersolutions. Thereafter, the prepared monomer solutions were treated for10 minutes by a power of 10 W, and were then maintained at 15° C. for 20minutes. Each of the DCDDA, TCDA and DCDA solutions was mixed with thepXDA solution at a volume ratio of 1:1 by injecting each of thesolutions into the pXDA solution using a micropipette. Further, each ofthe HMDA, EBA and DEB solutions was mixed with the DCDDA solution at avolume ratio of 1:1 by injecting each of the solutions into the DCDDAsolution using a micropipette.

The radial porous diacetylene particles formed in this way were measuredusing a scanning electron microscope (SEM) and then observed. Theresults thereof are shown in FIG. 10. As shown in FIG. 10, it can beascertained that radial porous diacetylene particles were formed onlywhen DCDDA having two carboxylic acid groups and a diacetylene group andPXDA having two amine groups and a benzene group were used.

As described above, the radial porous diacetylene particle according tothe present invention can easily detect chemical and biologicalmaterials harmful to the human body for a short period of time and hasvery high fluorescent intensity because it has pores having a highersurface area than that of a conventional polydiacetylene sensor. Since aconventional polydiacetylene sensor is sensitive to thermal stimuli, itmust be carefully treated. However, since the radial porous diacetyleneparticle of the present invention is not sensitive to thermal stimuli,it can be easily treated at room temperature.

Although the preferred embodiments of the present invention have beendisclosed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims

1. A radial porous diacetylene particle, which is synthesized byion-bonding a diacetylene-containing dicarboxylic acid or diaminemonomer represented by Formula 1 below with a diamine or dicarboxylicacid monomer represented by Formula 2 below:G-(A)_(x)-C≡C—C≡C—(B)_(y)-G   [Formula 1] wherein A and B are eachindependently selected from a substituted or unsubstituted alkyl groupof two or more carbon atoms, an ethylene oxide group, an amide group andan ester group, G is selected from COOH and NH₂, and x and y are eachindependently an integer of 1 to 20,Q-(D)_(m)-Z-(E)_(n)-Q   [Formula 2] wherein Z is selected from asubstituted or unsubstituted alkyl group of one or more carbon atoms, abenzene group, a cycloalkyl group, a pyridine group, a pyrimidine groupand a naphthalene group, D and E are each independently selected from asubstituted or unsubstituted alkyl group of one or more carbon atoms, abenzene group, a cycloalkyl group, a pyridine group, a pyrimidine groupand a naphthalene group, D, E and Z are different from each other, Q isselected from COOH and NH₂, m and n are each independently an integer of0 to 20, and G of Formula 1 above is different from Q of Formula 2above.
 2. The radial porous diacetylene particle according to claim 1,wherein the diamine or dicarboxylic acid monomer represented by Formula2 above is represented by Formula 3 below:Q-(H₂C)_(m)-C₆H₄-(CH₂)_(n)-Q   [Formula 3] wherein Q is selected fromCOOH and NH₂, and m and n are each independently an integer of 1 to 10.3. The radial porous diacetylene particle according to claim 1, whereinthe radial porous diacetylene particle has optical characteristics ofcolor transition and fluorescence-emitting.
 4. The radial porousdiacetylene particle according to claim 1, wherein the radial porousdiacetylene particle has a particle size of 50 nm˜50 μm and a pore sizeof 1 nm˜1 μm.
 5. A method of manufacturing a radial porous diacetyleneparticle, comprising the steps of: (a) respectively dissolving adiacetylene-containing dicarboxylic acid or diamine monomer representedby Formula 1 below and a diamine or dicarboxylic acid monomerrepresented by Formula 2 below in a solvent to prepare a solutionincluding the diacetylene-containing dicarboxylic acid or diaminemonomer and a solution including the diamine or dicarboxylic acidmonomer:G-(A)_(x)-C≡C—C≡C—(B)_(y)-G   [Formula 1] wherein A and B are eachindependently selected from a substituted or unsubstituted alkyl groupof two or more carbon atoms, an ethylene oxide group, an amide group andan ester group, G is selected from COOH and NH₂, and x and y are eachindependently an integer of 1 to 20,Q-(D)_(m)-Z-(E)_(n)-Q   [Formula 2] wherein Z is selected from asubstituted or unsubstituted alkyl group of one or more carbon atoms, abenzene group, a cycloalkyl group, a pyridine group, a pyrimidine groupand a naphthalene group, D and E are each independently selected from asubstituted or unsubstituted alkyl group of one or more carbon atoms, abenzene group, a cycloalkyl group, a pyridine group, a pyrimidine groupand a naphthalene group, D, E and Z are different from each other, Q isselected from COOH and NH₂, m and n are each independently an integer of0 to 20, and G of Formula 1 above is different from Q of Formula 2above; (b) ultrasonically treating each of the solutions; (c)maintaining each of the ultrasonically-treated solutions at roomtemperature; and (d) mixing the solution including thediacetylene-containing dicarboxylic acid or diamine monomer representedby Formula 1 above with the solution including the diamine ordicarboxylic acid monomer represented by Formula 2 above to form aradial porous diacetylene particle and then growing the radial porousdiacetylene particle.
 6. The method according to claim 5, wherein thesolvent is at least one selected from the group consisting oftetrahydrofuran (THF), chloroform, toluene, ethanol, isopropanol, andn-hexane.
 7. The method according to claim 5, wherein each of thesolution including the diacetylene-containing dicarboxylic acid ordiamine monomer represented by Formula 1 above and the solutionincluding the diamine or dicarboxylic acid monomer represented byFormula 2 above has a concentration of 10 mM˜50 mM.
 8. The methodaccording to claim 5, wherein each of the solution including thediacetylene-containing dicarboxylic acid or diamine monomer representedby Formula 1 above and the solution including the diamine ordicarboxylic acid monomer represented by Formula 2 above has aconcentration of 10 mM˜20 mM.
 9. The method according to claim 5,wherein the solution including the diacetylene-containing dicarboxylicacid or diamine monomer represented by Formula 1 above and the solutionincluding the diamine or dicarboxylic acid monomer represented byFormula 2 above are maintained at a room temperature of 5˜30° C. for 10minutes˜1 hour during a mixing process.
 10. The method according toclaim 5, wherein the solution including the diacetylene-containingdicarboxylic acid or diamine monomer represented by Formula 1 above andthe solution including the diamine or dicarboxylic acid monomerrepresented by Formula 2 above are maintained at a room temperature of10˜25° C. for 10 minutes˜1 hour during the process of mixing thesolution.
 11. The method according to claim 5, wherein the solutionincluding the diacetylene-containing dicarboxylic acid or diaminemonomer represented by Formula 1 above and the solution including thediamine or dicarboxylic acid monomer represented by Formula 2 above aremixed in a volume ratio of 1:0.2˜5.
 12. The method according to claim 5,wherein the ultrasonic treatment is carried out for 30 minutes by apower of 5˜20 W.